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High activity metal carbene metathesis catalysts generated using thermally activated N-heterocyclic carbene precursor

A heterocyclic carbene and catalyst technology, applied in the field of highly active metal carbene metathesis catalysts prepared by thermally activating N-heterocyclic carbene precursors

Inactive Publication Date: 2004-07-07
CALIFORNIA INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0023] And, Grubbs discloses in Organic Letters (1999), 1 (16), 953-956, the NHC species that is protected by alkoxy group and benzylidene ruthenium complex do not react in solvent at room temperature; When deprotected in situ at 60-80 °C, they are easily combined with RuCl 2 (PR 3 ) 2 (=CHR) reacts
However, isolation of these alkylene groups generally requires air-free and water-free conditions and multiple purification steps to remove displaced trialkylphosphine

Method used

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  • High activity metal carbene metathesis catalysts generated using thermally activated N-heterocyclic carbene precursor
  • High activity metal carbene metathesis catalysts generated using thermally activated N-heterocyclic carbene precursor
  • High activity metal carbene metathesis catalysts generated using thermally activated N-heterocyclic carbene precursor

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Effect test

example

[0160] Can be used with NHC-X 2 -The preferred examples of Y mixed Ru or Os initiators are as follows:

[0161]

[0162] Where M = Ru or Os.

[0163] X 1 And X 2 Represents any anionic ligand, independently selected from chlorine (Cl), bromine (Br), iodine (I), thiocyanate (SCN), cyanate (CN), carboxylate (OC(O)R), trifluoro Acetate (OC(O)CF 3 ), trifluoromethanesulfonate (O 3 SCF 3 ), triflimide(N(SO 2 CF 3 ) 2 ), acetylacetone (acac), alkoxide (RO), aryl ether (ArO) and tosylate (O 3 SC 6 H 4 CH 3 ).

[0164] X is a functional group that can bond with the metal center, and the functional group is also bound to the alkylene part of the initiator (the "initiation point" and the subsequent "catalyzed" ring opening reaction of the strained ring) through the carbon skeleton; and wherein X is selected From alkoxy (-OR), thiooxy (-SR), phosphine (-PR) 2 ), phosphine (-P(O)R 2 ), amido (-NR 2 ), arsenic (-AsR 2 ), (-Sb 2 ), ene (-CR=CR 2 ), alkyne (-CCR), carboxylate (-OC(O)R), aceta...

Embodiment 1

[0300] The mixture was heated to the starting temperature of 49 ℃, in s-ImesHCCl 3 In the presence of =0.0215g, use Ru716 =0.0361g to polymerize 50g of DCPD (containing 8% by weight of trimeric DCPD), DCPD:Ru:s-ImesHCCl 3 The ratio of reagents is 7500:1:1.

[0301] Result: the time required to reach the maximum temperature (T max )=81s. T max =227°C. Conversion rate measured by thermogravimetric analysis (TGA) = 97.35%. Glass transition temperature measured by thermal mechanical analysis (TMA) = 154°C. Residual monomer ratio (extracted with toluene at room temperature)=0.51%.

Embodiment 2

[0303] The mixture was heated to the starting temperature of 49 ℃, in s-ImesHCCl 3 In the presence of =0.0041g, use Ru716 =0.00677g to polymerize 50g of DCPD, DCPD:Ru:s-ImesHCCl 3 The ratio of reagents is 40,000:1:1.

[0304] Result: the time required to reach the maximum temperature (T max )=510s. T max =192°C. The conversion rate measured by thermogravimetric analysis (TGA) at 400°C under nitrogen = 87.53%. Glass transition temperature measured by thermal analysis method (TMA) = 105°C. Residual monomer ratio (extracted with toluene at room temperature) = 9.74%.

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Abstract

The invention provides a method of making a ruthenium or osmium carbene catalyst having an imidazolidine in the presence of an olefin with the application of energy. The resulting metal compound has two carbene ligands, one from the original carbene, the other from the imidazolidine. The imidazolidine has bulky protecting groups in the two positions adjacent to the carbene carbon. The method of making the imidazoline from the salt in the presence of a base and chloroform is also disclosed.

Description

[0001] This application claims the rights of U.S. Provisional Patent Application No. 60 / 278,311 filed on May 23, 2001. The title of the application is "High Activity Ru Alkylidene& Vinylidene Derivatives Suitable for Olefin MetathesisGenerated using a Thermally Deprotectable N-HeterocyclicCarbene"; it also requires 2001 U.S. Provisional Patent Application No. 60 / 288,680 filed on May 3, 2005, the title of the application is "High Activity Group 8 Alkylidene and Vinylidene Derivatives Suitable for Olefin Metathesis Generated using a The rmally Activated N-Heterocyclic Carbene (NHC) Precursor"; It also requires the rights and interests of the U.S. Provisional Patent Application No. "_" filed on March 1, 2002. The application is titled "Polymer Processing Methods and Techniques UsingPentacoordinated or Hexacoordinated Ruthenium or OsmiumMetathesis Catalysts". Reference is made here to the content of each application. Introduce. Background technique [0002] The metathesis catalyst has ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J23/46B01J27/24B01J31/00B01J31/18B01J31/24B01J37/34C07C6/04C07C6/06C07D233/00C07D233/02C07D233/54C07D233/56C07D233/58C07F15/00C08F4/44C08F4/80C08G61/08
CPCC07F15/002B01J31/2404B01J2531/825B01J23/462C07C6/06C07F15/0046B01J2231/543B01J23/466B01J31/2273B01J31/24C07C6/04B01J31/2265C07C2531/22B01J2531/821Y02P20/55
Inventor A·贝尔R·H·格鲁布斯J·P·摩甘J·L·穆尔
Owner CALIFORNIA INST OF TECH
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